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Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors

Abstract

Non-fullerene organic acceptors have attracted increasing attention in recent years. One of the challenges in the synthesis of non-fullerene organic acceptors is to tune the absorption spectrum and molecular frontier orbitals, affording low bandgap molecules with improved absorption of the near-infrared solar photons. In this paper, we present the synthesis, optoelectronic and photovoltaic properties of a series of dimeric perylene diimide (PDI) based non-fullerene acceptors. These PDI dimers are bridged by oligothiophene (T) from 1T to 6T. With the increase of the oligothienyl size, the highest occupied molecular orbital (HOMO) energy is raised from −5.65 to −5.10 eV, while that of the lowest unoccupied molecular orbit (LUMO) is kept constant at −3.84 eV, affording narrow bandgap from 1.81 to 1.26 eV. The absorption from the oligothiophene occurs between 350 and 500 nm, which is complementary to that from its bridged PDI units, leading to a wide spectral coverage from 350 to 850 nm. The optimal dihedral angle between the bridged two perylene planes is dependent on the oligothienyl size, varying from 5° to 30°. The solubility of the dimers depends on the oligothienyl size and can be tuned by the alkyl chains on the bridged thienyl units. The possible applications as the solution-processable non-fullerene organic acceptor is primarily studied using commercial P3HT as the blend donor. The photovoltaic results indicate that 1T, 4T and 6T all yield a higher efficiency of ∼1.2%, whereas 2T, 3T and 5T all give a lower efficiency of <0.5%. The difference in the cell performance is related with the tradeoff between the differences of absorption, HOMO level and film-morphology between these dimers.

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Correspondence to Chuanlang Zhan.

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Citation: Zhang X, Yao JN, Zhan CL. Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors. Sci China Chem, doi: 10.1007/s11426-015-5485-8

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Zhang, X., Yao, J. & Zhan, C. Synthesis and photovoltaic properties of low bandgap dimeric perylene diimide based non-fullerene acceptors. Sci. China Chem. 59, 209–217 (2016). https://doi.org/10.1007/s11426-015-5485-8

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Keywords

  • non-fullerene acceptor
  • organic photovoltaic cell
  • perylene diimide
  • solution-processed
  • bulk-heterojunction